25957-39-5

Basic information

• Product Name: 3-phenyloxirane-2-carboxylic acid
• Synonyms: Glycidic acid, 3-phenyl-, trans-; trans-3-Phenylglycidic acid
• CAS NO: 25957-39-5
• Molecular Formula: C₉H₇O₃*Na
• Molecular Weight: 164.158
• Mol File: 25957-39-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 346.8°C at 760 mmHg
• Flash Point: 147.2°C
• Density: 1.359g/cm³
• Vapor Pressure: 2.13E-05mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: 3-phenyloxirane-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyloxirane-2-carboxylic acid(25957-39-5)
• EPA Substance Registry System: 3-phenyloxirane-2-carboxylic acid(25957-39-5)

Safety Data

• Hazardous Substances Data: 25957-39-5(Hazardous Substances Data)

Upstream product

• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 121-39-1 ethyl cis-3-phenylglycidate 
• 121-39-1 ethyl 3-phenylglycidate 
• 54885-10-8 sodium (E)-3-phenylglycidate 
• 100-52-7 benzaldehyde 

Downstream Products

• 127053-48-9 Methyl (2R^*,3R^*)-3-phenyl-1H-aziridine-2-carboxylate 
• 129866-73-5 (2R,3R)-3-Phenyl-1-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-aziridine-2-carboxylic acid methyl ester 
• 119628-74-9 trans-(4S^*,5R^*)-2,2,2,4-Tetraphenyl-5-methoxycarbonyl-1,3,2-oxazaphospholidine 
• 135500-19-5 (2R,3R;2S,3S)-3-[3-(2-Quinolylmethoxy)-anilino]-2-hydroxy-3-phenyl propionic acid, sodium salt 

Relevant articles and documents

Synthesis of all four homochiral stereoisomers of methyl 3-phenyl-1H-aziridine-2-carboxylate

Sodium -E3-phenylglycidate (±)-2E was prepared using the Darzens' procedure. Classical resolution with 1-phenylethylamine afforded optically pure salts (+)-(2S,3R)-2E and (-)-(2R,3S)-2E. Alternatively, (±)-2E was converted into (±)-2Z by ring opening of ethyl ester (±)1E with hydrogen bromide, followed by recyclization and saponification. Classical resolution of (±)-2Z with ephedrine afforded optically pure salts (+)-(2S,3S)-2Z and (-)-(2R,3R)-2Z Treatment of the four sodium salts with sodium azide followed by esterification gave hydroxy azido esters 3, which were finally converted into the four homochiral stereoisomers of methyl 3-phenyl-1H-aziridine-2-carboxylate 5 in a reaction with triphenylphosphine and subsequent heating of the initially formed oxazaphospholidines 4.